Core-Tetrasubstituted Naphthalene Diimides by Stille Cross-Coupling Reactions and Characterization of Their Optical and Redox Properties

[摘要]：The palladium-catalyzed cross-coupling reaction of 2,3,6,7-tetrabromonaphthalene diimide with various aryl- and alkynylstannanes afforded a series of hitherto unknown tetraaryl- and tetraethynyl-substituted naphthalene diimides (NDIs). UV/Vis spectroscopic studies revealed that the absorption maxima of ethynyl-substituted NDIs are significantly bathochromically shifted compared to those of unsubstituted and tetraaryl-substituted NDIs. Cyclic voltammetry investigations showed that ethynyl substituents shift the reduction potentials of NDIs anodically, thus these NDI derivatives are interesting candidates for air-stable r-channel organic field-effect transistors.

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